Sodium phenylbutyrate
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Sodium phenylbutyrate (Buphenyl, Ammonaps, SPB11)
Effective Against
Phenylbutyrate is a prodrug. In the human body it is metabolized by beta-oxidation to phenylacetate. Phenylacetate conjugates with glutamine to phenylacetylglutamine, that is eliminated with the urine.
Cost
Cost of molecule from Tocris Bioscience: 55 USD (100 mg)
Cost of Sodium Phenylbutyrate powder from Scandinavian Formulas, Inc.: USD .05/100 mg or USD 500/Kg
Reported Routes of Synthesis
Treatment of benzene (I) with AlCl3 in at 50°C followed by the condensation with butyrolactone (II) in the presence of NaOH in H2O at 50-60°C affords the free acid of the title compound (1).
Synthesis of 4-phenylbutyric acid. WO 2002094756, CA 2447803, EP 1404638, JP 2004527577, US 6372938
Mono-decarboxylation of diester (I) by means of HCl in the presence of AcOH at reflux furnishes 4-phenylbutyric acid (II), which is finally treated with NaOH in H2O at 70°C or Na2CO3 in MeOH at 60°C or H2O at 90°C to afford the title compound (1,2).
Navinta LLC. Process for preparation of liquid dosage form containing sodium 4-phenylbutyrate. US 2007004805, WO 2007005633, EP 1901710, JP 2009500345
Navinta LLC & Tikvah Therapeutics, Inc. Process for preparation of liquid dosage form containing sodium 4-phenylbutyrate. WO 2008083226, US 2008171792